| 1. Round | 23/03/2019 | Louisville City FC | - | Hartford Athletic | 2:1 | ||||
| 2. Round | 21/04/2019 | Louisville City FC | - | Ottawa Fury | 1:0 | ||||
| 3. Round | 12/05/2019 | Birmingham Legion | - | Louisville City FC | 0:3 | ||||
| 6. Round | 04/08/2019 | Charlotte Independence | - | Louisville City FC | 0:1 |  |
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| 6. Round | 11/08/2019 | Louisville City FC | - | Atlanta United II | 5:1 |  |
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| 6. Round | 18/08/2019 | Charleston Battery | - | Louisville City FC | 1:2 | |
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| 6. Round | 24/08/2019 | Louisville City FC | - | North Carolina FC | 1:0 | |
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| 6. Round | 31/08/2019 | Louisville City FC | - | Indy Eleven | 1:1 | ||||
| 7. Round | 08/09/2019 | Pittsburgh Riverhounds | - | Louisville City FC | 0:0 | ||||
| 7. Round | 15/09/2019 | Hartford Athletic | - | Louisville City FC | 0:1 | ||||
| 7. Round | 22/09/2019 | Louisville City FC | - | New York RB II | 5:3 | ||||
| 7. Round | 29/09/2019 | Louisville City FC | - | Tampa Bay Rowdies | 2:2 | ||||
| 8. Round | 20/10/2019 | Memphis 901 | - | Louisville City FC | 1:2 |
USA